Lenny's Podcast: Product | Growth | Career Lenny Rachitsky

Kenneth Berger coaches startup leaders on how to prevent burnout, advocate for their desired lifestyle, and make a meaningful impact on the world. He’s spent more than 20 years in the tech industry, is a former founder backed by top investors, and was the first product manager at Slack. Kenneth’s core mission is to help startup leaders change the world by learning to ask for what they want, living with integrity, and building genuine relationships even with the people they find most challenging. Currently he is writing a book, Ask for What You Want, in which he aims to share his actionable strategies for creating change in the world. In our conversation, we explore:
• Why asking for what you want is so impactful
• Three steps to effectively ask for what you want
• Challenges that arise when people struggle to ask for what they want
• Why hearing “no” is a normal part of the process
• The “dream behind the complaint” technique for uncovering desires
• Kenneth’s experience of being fired three times from Slack
• How embracing fear and discomfort is key to getting what you want
• Why discipline is overrated
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Find the transcript at: https://www.lennysnewsletter.com/p/ask-for-what-you-want-kenneth-berger
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Where to find Kenneth Berger:
• X: https://twitter.com/kberger
• Threads: https://www.threads.net/@kberger
• LinkedIn: https://www.linkedin.com/in/kberger/
• Website: https://kberger.com/
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Kenneth’s background
(04:31) The importance of asking for what you want
(06:36) Challenges that arise when people struggle to ask for what they want
(08:09) A personal example of failing to ask for what you want
(09:17) Signs this is a skill you need to work on
(10:49) How to get better at knowing what you want
(15:28) Why hearing “no” is a normal part of the process
(17:29) Getting a “yes” vs. a “hell yes”
(19:20) Step 1: Articulate what you want
(24:07) Doing an integrity check
(26:56) Step 2: Ask for what you want intentionally
(30:45) Understanding your influence
(34:48) Using complaints as inspiration
(36:24) Internal family systems
(38:00) Giving feedback
(41:24) Step 3: Accept the response
(45:22) Kenneth’s experience of being fired three times from Slack
(57:30) Advice on being the first PM at a company or startup
(01:04:58) Contrarian corner: anti-discipline
(01:05:52) Lightning round
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Referenced:
• Joining as the first product manager: https://www.lennysnewsletter.com/p/joining-as-the-first-product-manager
• Internal Family Systems: https://ifs-institute.com/
• How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin
• Leaders in Tech: https://leadersintech.org/
• The Three Realities Framework | The 15% Rule | Feedback Guidelines: https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin
• T-group weekends at Stanford: https://www.gsb.stanford.edu/experience/learning/leadership/interpersonal-dynamics/facilitation-training-program/intro-tgroup
• DBT skill DEAR MAN: https://www.therapistaid.com/therapy-worksheet/dbt-dear-man
• Dialectical behavior therapy (DBT): https://my.clevelandclinic.org/health/treatments/22838-dialectical-behavior-therapy-dbt
• Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor
• Stewart Butterfield on LinkedIn: https://www.linkedin.com/in/butterfield/
• How to fire

Jag Duggal is chief product officer at Nubank, a decacorn neobank founded in Brazil. It’s valued at over $30 billion, is bigger than Coinbase, Robinhood, Affirm, and SoFi combined, has 100 million customers (more than Bank of America!) while only operating in three countries in Latin America, and 80% to 90% of its growth comes through word of mouth. Prior to Nubank, Jag was a director of product management at Facebook, a senior vice president at Quantcast, and a product leader at Google. In our conversation, we discuss:
• How Nubank builds a fanatical user base
• Tactics for driving word-of-mouth growth
• Measuring customer love through the Sean Ellis score
• The importance of strategic clarity
• The role of category design in creating successful products
• Why companies should strive to be “fundamentally different,” not “incrementally better”
• Nubank’s vision for an AI-powered banking future
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• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs
• Mercury—The powerful and intuitive way for ambitious companies to bank
• OneSchema—Import CSV data 10x faster
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Find the transcript at: https://www.lennysnewsletter.com/p/be-fundamentally-different-jag-duggal
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Where to find Jag Duggal:
• LinkedIn: https://www.linkedin.com/in/jagduggal/
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Jag’s background
(04:34) Nubank’s remarkable achievements
(06:01) Nubank’s product development process
(11:23) Nubank’s values
(12:16) Building products people love fanatically
(15:21) The Sean Ellis score
(21:27) An example project using the Sean Ellis score
(25:07) Picking up the phone and calling customers
(28:20) The importance of starting small and iterating
(30:42) Pushing back effectively
(34:10) Uncovering pain points through customer research
(37:53) An example of setting a clear hypothesis
(42:01) Developing a strategy
(52:16) “Be fundamentally different, not incrementally better”
(53:10) Category design
(57:37) Nubank’s founding story and goals for the future
(01:00:46) Advice for adding new product lines
(01:03:46) The future of fintech and banking
(01:09:23) AI corner
(01:12:34) Failure corner
(01:20:24) Key takeaways
(01:22:11) Lightning round
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Referenced:
• Nubank: https://nubank.com.br/en/
• Coinbase: https://www.coinbase.com/
• Robinhood: https://www.robinhood.com/
• SoFi: https://www.sofi.com/
• Affirm: https://www.affirm.com/
• Lemonade: https://www.lemfi.com/
• Bank of America: https://www.bankofamerica.com/
• Nubank achieves a world record with more than 7 million people participating in NuBolão in one month: https://building.nubank.com.br/nubank-achieves-world-record-with-nubolao
• Nu México carries out first financial transaction 20 meters under the depth of the sea: https://www.bnamericas.com/en/news/nu-mexico-carries-out-first-financial-transaction-20-meters-under-the-depth-of-the-sea
• David Vélez on LinkedIn: https://www.linkedin.com/in/david-v%C3%A9lez-1004875
• Cristina Junqueira on LinkedIn: https://www.linkedin.com/in/crisjunqueira
• Edward Wible on LinkedIn: https://www.linkedin.com/in/adamedwardwible
• Sequoia Capital: https://www.sequoiacap.com/
• Churrascaria: https://en.wikipedia.org/wiki/Churrascaria
• Nubank’s real foundation: our culture and values: https://building.nubank.com.br/nubank-culture-and-values/
• Working Backwards Press Release Template and Example: https://www.linkedin.com/pulse/working-backwards-press-release-template-example-ian-mcallister/
• Sean Ellis test: https://productcoalition.com/using-sean-ellis-test-for-measuring-your-product-market-fit-c8ac98053c2c
• How to know if you’ve got product-market fit: https://www.lennysnewsletter.com/p/how-to-know-if-youve-got-productmarket
• Reid Hoffman o

Vikrama Dhiman heads all things product at Gojek, including product management, design, program management, and research, across Indonesia, Singapore and India. He has over 16 years of experience building internet products, consults with Fortune 500 companies, and is among the most well-known and respected product leaders in all of Asia. In our conversation, we discuss:
• The most common traits among successful product managers
• The 3 W’s framework for PM career growth
• The Four A’s of leveling up in product management
• The right way to push back as a PM
• Common pitfalls that stall PM careers
• Vikrama’s advice for transitioning into product management
• Why intent alone is not enough
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• Uizard—AI-powered prototyping for visionary product leaders
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• Coda—The all-in-one collaborative workspace
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Find the transcript at: https://www.lennysnewsletter.com/p/a-framework-for-pm-skill-development
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Where to find Vikrama Dhiman:
• X: https://twitter.com/vikramadhiman
• LinkedIn: https://www.linkedin.com/in/vikrama/
• Website: https://www.vikramadhiman.com/
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Vikrama’s background
(03:56) Three common traits among great PMs
(07:09) The first W: What you produce
(15:40) The second W: What you bring to the table
(18:58) The third W: What’s your operating model?
(20:36) Three traits that make you a great PM to work with
(21:49) How to improve the quality and quantity of your outputs
(23:26) The art of the pushback
(26:55) Common factors that impede career growth
(33:39) Vikrama’s personal reflections
(39:33) Choosing which skill(s) to focus on developing
(46:28) The ambiguity of the PM role
(51:47) The 8 axis for PM growth
(56:57) Contrarian corner: Why intent alone is not enough
(59:30) Lightning round
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Referenced:
• Taxi mafias, cash vaults, and 100% MoM growth: The story behind Southeast Asia’s biggest startup | Kevin Aluwi (Gojek): https://www.lennysnewsletter.com/p/taxi-mafias-cash-vaults-and-100-mom
• How to scrappily hire for, measure, and unlock growth | Crystal Widjaja, Gojek and Kumu: https://www.lennysnewsletter.com/p/how-to-hire-for-measure-and-unlock
• Gojek: https://www.gojek.com/en-id
• SQL: https://en.wikipedia.org/wiki/SQL
• Oracle: https://www.oracle.com/
• Crystal Widjaja on LinkedIn: https://www.linkedin.com/in/crystalwidjaja
• Raditya Wibowo: https://www.linkedin.com/in/raditya-wibowo-a0845436/?originalSubdomain=id
• Sidu Ponnappa on LinkedIn: https://www.linkedin.com/in/sidup
• Leveraging mentors to uplevel your career | Jules Walter (YouTube, Slack): https://www.lennysnewsletter.com/p/leveraging-mentors-to-uplevel-your
• Kevin Aluwi on LinkedIn: https://www.linkedin.com/in/kaluwi/
• Workday: https://www.workday.com/
• Salesforce: https://www.salesforce.com/
• Small Data: The Tiny Clues That Uncover Huge Trends: https://www.amazon.com/Small-Data-Clues-Uncover-Trends/dp/1250080681
• Originals: How Non-Conformists Move the World: https://www.amazon.com/Originals-How-Non-Conformists-Move-World/dp/014312885X
• Thinking, Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555
• Miss Congeniality on Prime Video: https://www.amazon.com/Miss-Congeniality-Sandra-Bullock/dp/B002R5HQDK
• Schitt’s Creek on Prime Video: https://www.amazon.com/Schitts-Creek/dp/B083LDRW9F
• DramaBox: https://www.dramaboxapp.com/
• Am I Overthinking This?: Over-Answering Life’s Questions in 101 Charts: https://www.amazon.com/Am-Overthinking-This-Over-answering-questions/dp/1452175861/
• Crazy Rich Asians on Prime Video: https://www.amazon.com/Crazy-Rich-Asians-Constance-Wu/dp/B07JGJFXBF
• 9 Best Hawker Centers in Singapore—and What to Eat There: https://ww

Hamilton Helmer is one of the world’s leading experts on business strategy and the author of the seminal book 7 Powers: The Foundations of Business Strategy, which provides a comprehensive framework for understanding what it really takes to achieve and sustain a competitive advantage. With more than three decades of experience in the strategic consulting industry, Hamilton has advised over 200 companies—from burgeoning startups to Fortune 100 giants—on how to identify, build, and leverage their unique strategic powers. In our conversation, we discuss:
• Potential sources of power that startups should develop from an early stage
• Common misconceptions among companies about the types of power they possess
• How power relates to strategy
• The difference between a moat and a power
• Practical strategies for non-leaders to leverage insights about power and strategy in their work
• AI’s impact on competitive advantages and barriers to entry
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Brought to you by:
• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs
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• Paragon—Ship every SaaS integration your customers want
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Find the transcript and references at: https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer
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Where to find Hamilton Helmer:
• X: https://twitter.com/hamiltonhelmer
• LinkedIn: https://www.linkedin.com/in/hamilton-helmer-42983/
• Website: https://7powers.com/
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Hamilton’s background
(04:08) When power becomes important
(08:24) How strategy relates to power
(12:09) How power informs strategy
(14:46) The sequence of powers
(21:13) Common misconceptions
(24:39) Network effects vs. network economies
(26:58) Uber’s success
(29:16) Moats vs. powers
(31:12) Strategies for non-leaders to leverage power and strategy
(37:51) Advice on how to become a strategic thinker
(39:27) AI’s impact on the seven powers
(45:43) Why moving fast is not a power
(50:24) Three things that create value in a company
(51:16) The debt trajectory of the U.S.
(56:35) Optimism for the future
(59:25) Lightning round
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Referenced:
• 7 Powers: The Foundations of Business Strategy: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319
• John von Neumann: https://en.wikipedia.org/wiki/John_von_Neumann
• Pearl Harbor: https://www.history.com/topics/world-war-ii/pearl-harbor
• Where the Japanese Went Wrong at Pearl Harbor: https://pearlharbor.org/blog/where-japanese-went-wrong-pearl-harbor/
• The ‘7 Powers’ of business success—from one of Netflix’s early investors: https://www.qualitycompounders.com.au/post/the-7-powers-of-business-success-from-one-of-netflix-s-early-investors
• 7 Powers: Foundations of Business Strategy (Key Takeaways): https://www.linkedin.com/pulse/7-powers-foundations-business-strategy-key-takeaways-nikita-maloo/
• Strategy Capital: https://strategycapital.com/
• Warren Buffett: https://www.forbes.com/profile/warren-buffett/
• Charlie Munger: https://www.forbes.com/profile/charles-munger/
• Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://www.stripe.press/poor-charlies-almanack
• Bill Gates reveals why Warren Buffett was an invaluable source of support during the stormiest period of his career: https://www.businessinsider.com/bill-gates-interview-warren-buffett-support-microsoft-antitrust-lawsuit-2019-6
•  Billionaire Warren Buffett’s Secret Love Affair With Castles, Revealed: https://www.thestreet.com/opinion/billionaire-warren-buffett-s-secret-love-affair-with-castles-revealed-14290973
• Netflix didn’t kill Blockbuster—how Netflix almost lost the movie rental wars: https://www.cnbc.com/2020/09/22/how-netflix-almost-lost-the-movie-rental-wars

Annie Duke is a former professional poker player, a decision-making expert, and a special partner at First Round Capital. She is the author of Thinking in Bets (a national bestseller) and Quit: The Power of Knowing When to Walk Away and the co-founder of the Alliance for Decision Education, a nonprofit whose mission is to improve lives by empowering students through decision skills education. In our conversation, we cover:
• What Annie learned from the late Daniel Kahneman
• The power of pre-mortems and “kill criteria”
• The relationship between money and happiness
• The power of “mental time travel”
• The nominal group technique for better decision quality
• How First Round Capital improved their decision-making process
• Many tactical decision-making frameworks
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• LinkedIn Ads—Reach professionals and drive results for your business
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Find the transcript at: https://www.lennysnewsletter.com/p/making-better-decisions-annie-duke
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Where to find Annie Duke:
• X: https://twitter.com/AnnieDuke
• LinkedIn: https://www.linkedin.com/in/annie-duke/
• Website: https://www.annieduke.com/
• Substack: https://www.annieduke.com/substack/
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Annie’s background
(03:53) Lessons from Daniel Kahneman: humility, curiosity, and open-mindedness
(09:15) The importance of unconditional love in parenting
(15:15) Mental time travel and “nevertheless”
(20:06) The extent of improvement possible in decision-making 
(24:54) Independent brainstorming for better decisions
(35:36) Making sure people feel heard
(42:41) The “3Ds” framework to make better decisions
(44:49) Decision quality
(55:46) Improving decision-making at First Round Capital
(01:05:05) Using pre-mortems and kill criteria
(01:10:15) Making explicit what’s implicit
(01:10:55) The challenges of quitting and knowing when to walk away
(01:19:23) Where to find Annie
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Referenced:
• Daniel Kahneman, Who Plumbed the Psychology of Economics, Dies at 90: https://www.nytimes.com/2024/03/27/business/daniel-kahneman-dead.html
• Adversarial collaboration: https://en.wikipedia.org/wiki/Adversarial_collaboration
• Does more money correlate with greater happiness?: https://penntoday.upenn.edu/news/does-more-money-correlate-greater-happiness-Penn-Princeton-research#
• Income and emotional well-being: A conflict resolved: https://pubmed.ncbi.nlm.nih.gov/36857342/
• Strategic decisions: When can you trust your gut?: https://www.mckinsey.com/capabilities/strategy-and-corporate-finance/our-insights/strategic-decisions-when-can-you-trust-your-gut
• Cass Sunstein on X: https://twitter.com/CassSunstein
• Dr. Becky on Instagram: https://www.instagram.com/drbeckyatgoodinside
• A framework for finding product-market fit | Todd Jackson (First Round Capital): https://www.lennysnewsletter.com/p/a-framework-for-finding-product-market
• First Round Capital: https://firstround.com/
• Brett Berson on X: https://twitter.com/brettberson
• Renegade Partners: https://www.renegadepartners.com/
• Renata Quintini on X: https://twitter.com/rquintini
• Roseanne Wincek on X: https://twitter.com/imthemusic
• Josh Kopelman on X: https://twitter.com/joshk
• Bill Trenchard on X: https://twitter.com/btrenchard
• Linnea Gandhi on X: https://twitter.com/linneagandhi
• Maurice Schweitzer on X: https://twitter.com/me_schweitzer
• Problems with premortems: https://sjdm.org/presentations/2021-Poster-Gandhi-Linnea-debiasing-premortem-selfserving~.pdf
• Create a Solid Plan on How to Fail Big This Year: https://www.forbes.com/sites/forbesfinancecouncil/2020/02/07/create-a-solid-plan-on-how-to-fail-big-this-year/
• Quit: The

Kayvon Beykpour was the longest-serving head of product at Twitter and was GM of Twitter’s consumer division until the platform was acquired by Elon Musk. He originally joined Twitter in 2015 through the acquisition of his company, Periscope, the largest live video streaming platform at the time. Periscope pioneered technology that inspired Instagram Live, TikTok Live, Facebook Live, and other social networks’ expansion into video streaming. In our conversation, we discuss:
• The story of being let go from Twitter after Elon’s acquisition
• How he turned Twitter’s stagnant culture around
• Kayvon’s thoughts on the limitations of frameworks like Jobs to Be Done
• Why Periscope failed
• Advice for building consumer products
• When to copy, when to innovate
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Brought to you by:
• Enterpret—Transform customer feedback into product growth
• OneSchema—Import CSV data 10x faster
• Heap—Cross-platform product analytics that convert, engage, and retain customers
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Find the transcript at: https://www.lennysnewsletter.com/p/twitters-former-head-of-product-kayvon-beykpour
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Where to find Kayvon Beykpour:
• X: https://twitter.com/kayvz
• LinkedIn: https://www.linkedin.com/in/kayvz/
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Kayvon’s background
(04:31) Getting Elon up to speed at Twitter
(11:34) The story of being let go from Twitter after Elon’s acquisition
(21:09) Changing the product culture at Twitter
(29:44) Building the “hide replies” feature
(32:02) Sacred crows, taking bold bets, and reigniting growth
(34:28) Aquihires and their impact
(42:40) Tips for successful acquisitions and staffing
(47:00) The limitations of frameworks like JTBD
(53:20) Signs you’ve gone too far with a framework
(57:44) Lessons from building Periscope
(01:00:41) Reasons why Periscope failed
(01:07:24) The challenges of implementing video at Twitter
(01:12:05) Copying ideas in good taste
(01:17:58) How to get better at building consumer products
(01:19:51) What Kayvon is building
(01:20:31) Lightning round
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Referenced:
• Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennyspodcast.com/lessons-on-building-product-sense-navigating-ai-optimizing-the-first-mile-and-making-it-through-t/
• What it’s like to sell your startup for ~$120 million before it’s even launched: Meet Twitter’s new prized possession, Periscope: https://www.businessinsider.com/what-is-periscope-and-why-twitter-bought-it-2015-3
• Walter Isaacson on LinkedIn: https://www.linkedin.com/in/walter-isaacson-b8b81520/
• Elon Musk on X: https://twitter.com/elonmusk
• Parag Agrawal on LinkedIn: https://www.linkedin.com/in/parag-agrawal-5a14742a/
• Jack Dorsey on LinkedIn: https://www.linkedin.com/in/jack-dorsey-a43b07242/
• Blackboard: https://en.wikipedia.org/wiki/Blackboard_Inc.
• Keith Coleman on X: https://twitter.com/kcoleman
• Esther Crawford on LinkedIn: https://www.linkedin.com/in/esthercrawford/
• Twitter acquires Chroma Labs: https://tech.hindustantimes.com/tech/news/twitter-acquires-chroma-labs-story-aqvcRPAoYXqXJuAbefA6cN.html
• John Barnett on LinkedIn: https://www.linkedin.com/in/johnbarnettt/
• Jobs to Be Done framework: https://jobs-to-be-done.com/jobs-to-be-done-a-framework-for-customer-needs-c883cbf61c90
• Hot takes and techno-optimism from tech’s top power couple: https://www.lennyspodcast.com/hot-takes-and-techno-optimism-from-techs-top-power-couple-sriram-and-aarthi/
• Nike Is Unveiling the Kobe 11 Tomorrow Using Periscope: https://sneakernews.com/2015/12/13/nike-is-unveiling-the-kobe-11-tomorrow-using-periscope/
• Chris Sacca’s website: https://chrissacca.com/
• Facebook Live: https://www.facebook.com/formedia